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Portland’s Indie Boutique Tour

Take a fashionista's day trip around town.

Here’s a familiar scenario: Your best friend from college is finally coming to visit. She’s never been to Portland — or Oregon, for that matter — and she wants to check out what all the hype is about. This woman is a true fashionista, so she’s going to want to hit the local boutiques. Where to take her?

I’ve been a personal stylist in Portland for more than 11 years, and I hear this story all the time. Here’s a day trip of local boutiques with stops along the way to enjoy Portland’s delicious food and drink.

AlbertaStart the day with a Champagne cocktail and a brioche at Petite Provence on Northeast Alberta Street. Begin your adventure at Garnish, a unique boutique with handmade items that are contemporary, wearable pieces of artwork. Then cruise up to Tumbleweed Boutique to scope out the clothing line Kara-line, a favorite of local women. The dresses are made with the most beautiful of fabrics and are cut to flatter a woman’s shape.

NortheastNext, head over to Northeast 42nd Avenue and Northeast Fremont Street to Shop Adorn for nationally acclaimed local design labels such as the Portland Collection from Pendleton Woolen Mills, with their distinguishable cardigans, separates and accessories.

Shop Adorn also carries Prairie Underground, a casual but contemporary label of pieces that you won’t want to take off. Don’t leave without picking up one of the Ellington handbags, especially if you’re looking for a well-made, well-priced, everyday bag.

Amenity Shoes is right around the corner. They carry some of the finest shoe brands with an emphasis on exceptional quality, great design and comfort. Who doesn’t love a pair of shoes that are gorgeous and comfortable?

SoutheastYou’ve probably worked up an appetite by now. Cool your jets and treat yourself to a margarita and fresh tacos at ¿Por Qué No? Taqueria on Southeast Hawthorne Boulevard.

You’ll find several fantastic boutiques on and around this street, including Buffalo Exchange, a consignment store, and Imelda’s Shoes and Louie’s Shoes for Men. Don’t miss Communion, where you can shop for the man in your life (and you’ll probably find something for yourself, too). Cassidy Jewelry has a great selection and excellent prices. You’ll find something to wear every day as well as something original for that special event. Presents of Mind, a novelty shop, is the place for high-quality, memorable souvenirs that will actually be appreciated, even coveted. Pick up a stylish T-shirt with the silhouette of one of our iconic bridges or an “I Love Oregon” duct-tape wallet.

DowntownHop on one of our famous bridges and head across the Willamette River to Pioneer Courthouse Square, the heart of the city, to start your shopping on the west side. Before you hit the stores, grab a cup of coffee, take a seat on the steps of the Square and people-watch for a bit. It’s truly a melting pot of locals, as well as visitors, and there is always something going on in the Square.

Once you’re caffeinated, walk a couple of blocks up to Parallel on Southwest Washington Street. Here you’ll see high-end, gorgeous minimalist pieces that no city girl can live without. Frances May, across the street, is a must visit. They carry the finest of local talent, plus labels such as Rick Owens and Rachel Comey.

Northwest 23rd AvenueLast stop for shopping is Portland’s beloved Northwest 23rd Avenue. The street has such charm, especially in the fall and winter, when the holiday lights are up and twinkling. Check out national retailers like Free People and prAna, but don’t miss the locally owned stores that give this street its personality. Gilt carries the largest selection of vintage and antique jewelry in the entire Pacific Northwest. Sloan Boutique and their sister store, plaTform, are go-tos for retail therapy; you can find an armful of exciting pieces without breaking the bank.

At this point, you’re likely to be all shopped out. Head to Jo Bar & Rotisserie, a cozy restaurant and bar where you can find the best gourmet burger in town. End your epic day with a dessert from Papa Haydn next door. Get the toffee cheesecake — it’s heaven in a bite.

Portland has so many amazing boutiques, and this tour should give your guest a taste of what our talented city has to offer. Be prepared, though: After this day of shopping, she’ll certainly be back.

These maps and directions are for planning purposes only. You may find that construction projects, traffic, or other events may cause road conditions to differ from the map results. For travel options, weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941.

When the sky is full of fluffy flakes and the mountains are covered with a white blanket of snow, what’s the best way to have fun in Oregon? We asked and you answered. Here are nine of our readers’ favorite ways to celebrate winter in Oregon.

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